Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines

Sujin Park; Youngeun Jung; Ikyon Kim

doi:10.1016/j.tet.2014.08.003

Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines

Sujin Park, Youngeun Jung, Ikyon Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

Abstract

Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein.

Original language	English
Pages (from-to)	7534-7550
Number of pages	17
Journal	Tetrahedron
Volume	70
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2014.08.003
Publication status	Published - 2014 Oct 14

Bibliographical note

Funding Information:
This research was supported in part by Nano Material Technology Development Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology . We also thank Yonsei University for partial financial support of this work through the Yonsei University Global Specialization Project of 2014.

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.08.003

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title = "Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines",

abstract = "Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein.",

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doi = "10.1016/j.tet.2014.08.003",

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AU - Jung, Youngeun

AU - Kim, Ikyon

N1 - Funding Information: This research was supported in part by Nano Material Technology Development Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology . We also thank Yonsei University for partial financial support of this work through the Yonsei University Global Specialization Project of 2014. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

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Y1 - 2014/10/14

N2 - Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein.

AB - Diversity-oriented synthesis of a chemical library based on a pyrrolo[1,2-a]pyrazine core is described by using palladium-catalyzed direct C6 arylation of pyrrolo[1,2-a]pyrazines with various aryl bromides. The starting materials, pyrrolo[1,2-a]pyrazines, were easily synthesized by the base-mediated N-alkylation of pyrrole-2-carboxaldehyde with several 2-bromoacetophenones followed by dehydrative cyclization with incorporation of nitrogen by the action of ammonium acetate. Introduction of other functional groups on this chemical scaffold is also discussed herein.

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Diversity-oriented decoration of pyrrolo[1,2-a]pyrazines

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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